1,3,4,5,6,11a-Hexahydro-7E-2-benzothionine 5, which is a [2,3] sigmatropic rearrangement product of 2-phenyltetrahydrothiopyranium 1-methylide 8, has been synthesized by reaction of 1-methyl-2phenyltetrahydrothiopyranium triflate 3 with sodium amide in liquid ammonia or by the fluoride ioninduced desilylation of trans-2-phenyl-1-[(trimethylsilyl)methyl]tetrahydrothiopyranium perchlorate trans-7...

Madhavan Jaccob , Gopal Sabapathi, J Vijaya Sundar, P Kolandaivel *, V Subramanian * & Ponnambalam Venuvanalingam * Theoretical and Computational Chemistry Laboratory, School of Chemistry, Bharathidasan University, Tiruchirappalli 620 024, Tamil Nadu, India Email: [email protected] Chemical Laboratory, CSIR-Central Leather Research Institute, Adyar, Chennai 600 020, Tamil Nadu, India Ema...

A facile and efficient synthetic protocol was established for the construction of novel tri- and tetra-cyclic pyrrolo/pyrrolizinoquinoline architectures via the in situ formation of azomethine ylide followed by an intramolecular [3 + 2] cycloaddition reaction strategy. This protocol leads to the creation of two/three new rings and three/four contiguous stereocentres, in which one of them is a t...

In this study, the excellent scalability of flow chemistry was shown. Selective formation of mono-bromoketones was chosen as a model reaction. In a full multivariate optimization experiment, 60 different settings for reaction parameters such as temperature and reaction time were screened, requiring only small amounts of chemicals. A mathematical model of the data was obtained and an optimum set...

The synthesis of spirocyclic amide acetals (33–93 %) has been achieved through Ru(II)-catalyzed condensations N-carbamate protected pyrrolidinones with metal carbenes derived from α-diazo-β-ketoesters. Thanks to the mildness diazo decomposition conditions induced by a 1 : combination [CpRu(MeCN)3][BArF] and 1,10-phenanthroline, formation sensitive products is possible. Full characterization thi...

Abstract Versatile, two-step syntheses of dihydrodibenzo[c,e]azepines, carbazole derivatives, and other alkaloid-type drug-like scaffolds by in situ generated azomethine ylide-induced intramolecular electrocyclization reaction from commercially available materials are presented. The mechanisms transition-metal-free carbon–carbon bond formation the role kinetic control, resulting good regioselec...

The Rh(II)-catalyzed coupling of chiral 2-thiopyranylindoles with vinyl diazoacetates results in the generation of indolines having quaternary substitution at C3 in high diastereoselectivity.